Pyrazole → 6-(6-chloro-pyrimidine-4-carbonyl)-3-methyl-4-pyrazol-1-ylmethyl-3H-benzoxazol-2-one

HRID 469340Notes

Reaction equation

HRID 469340 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([C:10]2[CH:20]=[C:19]([CH3:21])[C:13]3[N:14]([CH3:18])[C:15](=[O:17])[O:16][C:12]=3[CH:11]=2)=[O:9])[CH:3]=1.BrN1C(=O)CCC1=O.[N:30]([C:37]([CH3:41])(C)C#N)=[N:31][C:32](C)(C)C#N.N1C=CC=N1.CCN(C(C)C)C(C)C>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([C:10]2[CH:20]=[C:19]([CH2:21][N:31]3[CH:32]=[CH:41][CH:37]=[N:30]3)[C:13]3[N:14]([CH3:18])[C:15](=[O:17])[O:16][C:12]=3[CH:11]=2)=[O:9])[CH:3]=1

Participants

7

Reactant 5

HCID 1048PyrazoleHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 81531DiisopropylethylamineHCID 581811626-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Product 1

HCID 581812156-(6-chloro-pyrimidine-4-carbonyl)-3-methyl-4-pyrazol-1-ylmethyl-3H-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Under a nitrogen atmosphere 0.15 g (0.49 mmol) 6-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one, 95 mg (0.53 mmol) N-bromosuccinimide and 5.0 mg (30 mmol) 2,2′-azobis-isobutyronitrile (AIBN) in 15 mL carbon tetrachloride were combined and refluxed for 4 h. The precipitate formed was filtered off and the filtrate was combined with 20 μL isopropanol. After brief stirring 36 mg (0.53 mmol) pyrazole and 0.17 mL (0.99 mmol) DIPEA were added and the mixture was refluxed for 6 h. Then the reaction mixture was filtered through silica gel and washed with DCM/EtOAc (1/1). The filtrate was evaporated down i. vac. and the residue was reacted further as the crude product.

Workup

  1. temperaturerefluxed for 4 h
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. additionwere added
  5. temperaturethe mixture was refluxed for 6 h
  6. filtrationThen the reaction mixture was filtered through silica gel
  7. washwashed with DCM/EtOAc (1/1)
  8. customThe filtrate was evaporated down i
  9. customand the residue was reacted further as the crude product

Sources & evidence

ORD record
ord-a55f7359af6f46b4a66a163ef19e20c3
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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